This proposal involves studies for the synthesis of the antitumor agent antibiotic 593 A. This antibiotic is a naturally-occuring nitrogen mustard and structurally is the piperazinedione of a new amino acid, streptolutine. Key methods to be studied in the synthesis are (1) coupling of an optically active dialkylcooper lithium reagent, derived from (S)-malic acid, with appropriate alpha, beta-dehydroamino acids, (2) introduction of the Beta-amino function by Curtius reaction or by Michael addition, (3) introduction of chirality by stereospecific reduction of a dehydroamino acid, and (4) formation of the piperidine ring by cyclization involving an amine function. Analogs will be prepared that have sulfur and N-alkyl groups introduced into the molecule.